Derivatives of parabanic acid



Patented Mar. 8, 1949 DERIVATIVES OF PARABANIC ACID Kermit D. Longley, Philadelphia, Pa., assignor to Quaker Chemical Products Corp., Conshohocken, Pa., a corporation of Pennsylvania No Drawing. Application December 26, 1944, Serial No. 569,906

2 Claims.

The invention relates to derivatives of parabanic acid and more particularly relates to derivatives of parabanic acid which are suitable for waterproofing textile materials. The invention includes the process of treating textile materials therewith and textile materials so treated.

An object of the invention is to provide novel, inexpensive and efficient compositions for imparting durable, water repellent finishes to textile materials.

Another object is to provide new and useful compounds.

Other objects and advantages of the invention will become apparent as the following detailed description progresses.

In accordance with one embodiment of this invention, I react a long chain alkyl urea having more than six carbon atoms on the alkyl group with oxalic acid in the presence of a phosphorous halide, or I may react a long chain alkyl urea with an oxalic acid ester in the presence of a sodium alcoholate such as sodium ethylate, sodium methylate, or the like. The long chain parabanate so produced is dispersed in a cold alkali solution. This solution or dispersion forms a textile treating bath. Cloth may be immersed in this solution, passed through a wringer to remove excess solution, and the coated and impregnated cloth then dried at a temperature substantially above room temperature, for example, about 100 C. The heat of the drying decomposes the alkyl parabanate, depositing the aliphatic nucleus on the fabric. There is thus produced on the fabric a highly resistant finish Which is water insoluble and also insoluble in dry cleaning solvents.

The reaction involved in the above processes is illustrated by the following formula and equations, wherein R in the formula represents an alkyl group having more than six carbon atoms in a straight chain.

deposition on fabric of The preferred parabanates of this invention have the following probable formula:

where R. is an aliphatic group having above six carbon atoms and preferably from ten to eighteen carbon atoms, and R is a hydrogen, an aliphatic or aromatic group, or an aliphatic or aromatic group containing a hydrophilic group such as -05, SO3Na, CO.

The following example is given to illustrate the invention:

Octadecyl parabanate was made as follows:

Forty grams of an ethyl alcoholate containing 2.5 grams of Na metal were placed in a flask fitted with a sealed stirrer and a trap having a. return on it.

To this was added 31 grams of Octadecyl urea and 15 grams of diethyl oxalate. The alcohol was then distilled off and the pasty mass heated to 140 C. and maintained there for one hour. Because of the difficulty of agitation it is not felt that a large amount of the parabanate was obtained. When the heating was discontinued and the temperature had fallen sufficiently the alcohol was returned to the product.

The finished product is a soft, rather dry paste.

A 10% solution of this product (approximately 5% solids) was made. It is not readily dispersible in water alone, but is in ammoniacal solutions.

Cloth was immersed in this solution, passed through the wringer and dried. A spray test of fifty was obtained.

This fabric was then immersed in 10% NH4OH solution three times and dried each time. A spray test of eighty was obtained. This fabric was then washed vigorously with soap, rinsed and again dried. A spray test of seventy-five was obtained.

While I have described certain preferred embodiments of my invention, many modifications thereof may be made without departing from the spirit of the invention; and I do not wish to be limited to the detailed examples, formulas and. proportions of ingredients herein set forth, but desire to avail myself of all changes within the scope of the appended claims.

I claim:

1. An alkyl parabanate wherein the group attached to one nitrogen atom contains more than nine carbon atoms and the other nitrogen atom is attached to a group selected from the group consisting of hydrogen, an aliphatic group, an aromatic group, an aliphatic group containing a hydrophilic group, andv an aromaticgroup containing a hydrophilic group.

2. As a new compound, octadecyl parabanate.

KERMIT D. LONGLEY.

REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS Number Name Date 934,034 Boyeux Sept. 14, 1909 1,861,458 Sobotka June 7, 1932 10 2,186,628 Dickey Jan. 9, 1940 OTHER REFERENCES Monatschefte ffir Chemi'e, vol. 30., page 722. (Copy in Dept. of Agriculture Library, Washington, D. C.) 

